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Cheap flights from New York to Chicago from $155

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
NYC — CHI
6 Sep — 13 Sep1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from New York to Chicago are usually found in January or February, booked 83 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap flight deals from New York to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from New York to Chicago
Explore the most affordable flight options available from New York to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 7 August 2026.

Wed 26/807:30 -
Nonstop2h 43m
Wed 2/907:05 -
Nonstop2h 17m
Deal found 3/8$308
Sat 5/906:50 -
Nonstop2h 46m
Sat 5/920:36 -
Nonstop2h 23m
Deal found 4/8$310
Sat 14/1111:30 -
1 stop13h 20m
Tue 17/1114:03 -
1 stop6h 25m
Deal found 2/8$320
Mon 24/821:45 -
Nonstop2h 37m
Wed 2/912:16 -
Nonstop2h 21m
Deal found 3/8$322
Tue 8/907:30 -
Nonstop2h 43m
Wed 30/909:00 -
Nonstop2h 26m
Deal found 6/8$330
Sat 5/911:15 -
Nonstop2h 44m
Sun 13/906:00 -
Nonstop2h 13m
Deal found 7/8$337
Tue 8/910:42 -
Nonstop2h 44m
Sat 12/906:29 -
Nonstop2h 20m
Deal found 5/8$339
Tue 29/921:45 -
Nonstop2h 36m
Mon 5/1021:35 -
Nonstop2h 22m
Deal found 6/8$344
Fri 28/807:30 -
Nonstop2h 43m
Sun 30/821:35 -
Nonstop2h 22m
Deal found 7/8$351
Fri 18/905:23 -
Nonstop2h 50m
Fri 25/920:38 -
Nonstop2h 21m
Deal found 4/8$352
Tue 6/1017:29 -
Nonstop2h 59m
Tue 13/1006:43 -
Nonstop2h 23m
Deal found 5/8$354
Wed 19/809:15 -
Nonstop2h 43m
Wed 23/921:35 -
Nonstop2h 22m
Deal found 5/8$358

Find flight deals from New York to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from New York (NYC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 7 August 2026.

Round-trip from

$308

One-way from

$155

Popular in

June

Cheapest in

January

Average price

$413
United Airlines
  • United Airlines
  • 26/8-2/9
  • Nonstop
  • 5h 00m total
  • New York to Chicago
Search Deals
United Airlines
  • United Airlines
  • 25/8
  • Nonstop
  • 2h 37m total
  • New York to Chicago
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($110 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average return price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

Cheapflights Fare Finder

 
Customise your flight search to find flights from New York to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 7 August 2026.
Use the filters below to find and compare flights from New York to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Wed 16/9

11:15-12:59

Nonstop2h 44m

Chicago O'Hare Intl

Wed 23/9

13:30-16:54

Nonstop2h 24m

$337

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Wed 30/9

06:00-10:37

1 stop5h 37m

Chicago O'Hare Intl

Wed 30/9

17:10-23:15

1 stop5h 05m

$379

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 21/9

15:38-23:08

1 stop8h 30m

Chicago O'Hare Intl

Mon 28/9

15:00-23:06

1 stop7h 06m

$393

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Wed 19/8

06:00-12:16

1 stop7h 16m

Chicago O'Hare Intl

Sat 22/8

18:00-23:56

1 stop4h 56m

$408

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Mon 24/8

13:05-14:45

Nonstop2h 40m

Chicago O'Hare Intl

Sun 30/8

05:00-08:14

Nonstop2h 14m

$450

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sat 26/9

07:55-09:40

Nonstop2h 45m

Chicago O'Hare Intl

Mon 28/9

19:52-23:15

Nonstop2h 23m

$450

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Tue 1/9

09:15-10:58

Nonstop2h 43m

Chicago O'Hare Intl

Tue 15/9

08:40-11:58

Nonstop2h 18m

$450

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Sat 22/8

18:20-20:07

Nonstop2h 47m

Chicago O'Hare Intl

Wed 26/8

15:55-19:25

Nonstop2h 30m

$450
Fastest return journey

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Fri 11/9

23:00-00:28

Nonstop2h 28m

Chicago O'Hare Intl

Mon 14/9

21:35-00:57

Nonstop2h 22m

$464

NewarkChicago

EWR Newark - ORD Chicago O'Hare Intl

EWRORD

Newark

Thu 17/9

06:00-07:41

Nonstop2h 41m

Chicago O'Hare Intl

Sun 20/9

06:00-09:13

Nonstop2h 13m

$464

Flights are sorted by cheapest return flights first.

Deals found on 6/8

Showing 1-10 of 22 resultsSorted by cheapest first
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Best time to book a flight from New York to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from New York with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New York to Chicago

What is the cheapest month to book a flight from New York to Chicago?

Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $268). Flying from New York to Chicago in June is currently the most expensive (average of $487). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from NYC to CHI?

Find hourly flight availability from New York to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 7 August 2026.

When flying from New York to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 83% versus a flight in the afternoon.

Weekly flight availability from New York to Chicago

Explore weekly flight availability from New York to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 7 August 2026.

The most flights from NYC to CHI are scheduled on a Thursday (199 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (81 on average).

How much does it cost for a return flight from New York to Chicago?

Airfare is below average for this route at the moment.
New York to Chicago flights typically cost between $315 and $541 in August.
The cheapest return price found within the last 5 days was $308 on United Airlines (26 Aug–2 Sept).

How often are flights from New York to Chicago delayed?

About 19% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 155 minutes.

What is the most punctual flight time for New York to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on New York to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

How far ahead should I book a flight from New York to Chicago?

The best time to book flights from New York to Chicago is 63 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Related info for your journey

Find useful and relevant information for your journey from New York to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New York to Chicago?

    Airlines like United Airlines, Delta, and JetBlue fly from New York to Chicago in about 2h 44m. The time it takes to get you to your destination can typically vary by up to 5h 46m. New York and Chicago are separated by a distance of 1152 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the most reliable airlines from New York to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from New York to Chicago on time: Malaysia Airlines (87%), American Airlines (86%), Alaska Airlines (85%).

  • Can I find deals for flights from New York to Chicago that include hotel bookings?

    Yes. In addition to deals on New York to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from New York to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New York to Chicago.

  • Can I find deals for business class flights from New York to Chicago?

    Yes. Cheapflights offers flight deals from New York to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New York to Chicago?

    Currently, January is the cheapest month in which you can book a flight from New York to Chicago (average of $268). Flying from New York to Chicago in June is currently the most expensive (average of $487). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for New York to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from New York to Chicago?

Cheapflights makes it easy to find New York to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from New York to Chicago?

Cheapflights helps you find that perfect flight to Chicago from New York by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from New York to Chicago with no change fees?

Yes, we can. To see specific flights from New York to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from New York to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from New York today and book when prices fit your budget.

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